I am not sure I understand the question...

In all, it's all easy at this point. I know I can get there knowing the available tools.

Things I have done in the past that are a little rusty, yet I could pick back up in 5 minutes -- Databases, socket programming

Things I've beat to death recently -- Data serialization between various apps, Perl/Tk, build systems (a close cousin to system administration, but not quite the same)

Things I haven't completely explored yet, but easy just the same -- large-scale O.O. in Perl (haven't needed it for what I do at work other than some module exploitation). This is allright though, since I'm biased against most large-scale OO designs because they make some things too hard/complex, and I use Perl to escape pain, not create it.

I've only found a few things "hard" per se, like trying to write my own Parse::RecDescent grammar. The hype in this monastary towards this module makes me think a few people know what it is, but most are using it for very simple record parsing.

Summary: Perl makes the hard things easy and the impossible things possible. That's why I like the language. A beginner is going to have trouble only in learning the ins-and-outs of the language, how things are done in a Perlish way, and how to check his desire to go into full-hog obfuscation-show-off-mode. Once he gets to the level where he understands the dark corners, it will all be easy, or at least doable.

Now ask me to do half the Perl things in Java (a language that I know well, btw) and I'd have to say many of those things are still quite hard and require building a lot of infrastructure. The "Swiss Army Chainsaw" is infinitely useful everywhere!